D8 with a Question, Mark

Victoria is one of the new friends I made since coming home from Atlanta. She’s a groovy woman- wife, mother, and all around genuine person. And she’s absolutely beautiful. On one sunny Saturday morning while walking the market at Union Square, she said a five-word sentence to me; one that I’m not accustomed to hearing.

“I have someone for you…”

You know that feeling of dread combined with intrigue? That was my reaction. Of course, I wanted every detail about this someone. His name was Mark, and she’s known him for years. He was very successful in his career, Jewish, and she thought we’d make an amazing couple. Victoria said that he was also very handsome, age appropriate (he was in his early 50s) and was total boyfriend material- and more.

How could I say no?

After a few failed attempts at connecting, Mark and I had a very nice conversation. I emailed me a couple pictures, and he was definitely as Victoria described. We set a date for Thursday night.

We decided to meet on 53rd and Ninth and go from there; sort of a first date adventure. As he approached me, he was on his iPhone discussing a business deal. He gave me a big smile, and continued talking. He continued talking for ten minutes. When he finally hung up, he apologized for the call and we started our date. We decided to grab a burger and a beer. We chose a place quiet enough to have a great conversation.

And the conversation was exactly where the problems started. I would ask Mark a question, and get a short answer without those additions that a conversation needs to flow. It was like talking to a vault- nothing was coming out. From college to hobbies to family, Mark was on tighter lockdown than Fort Knox. He wouldn’t even tell me his birthday.

Ninety minutes later the date ended and I was exhausted from single-handedly carrying our NONversation. Mark thanked me for a great time, gave me a kiss, and said that we should do it again.

Really? Another night of failed attempts to converse with Mark seems about as appealing and rewarding as asking the Great Wall of China his thoughts on existing trade policies. The whole thing left me with several questions… Maybe Mark was nervous? Maybe his head was still in the conversation he was having on the phone when me met? Maybe his last date used his birthday date and other personal information to gain access to his Amex? Any way I looked at it, Mark just seemed not to be very open, which came across as his being extremely distrustful of me.

A few days later I was at Victoria’s apartment enjoying some coffee and blueberry pie. She wanted every detail of the date. I really tried to be nice about the description…

“Well… he really didn’t say much. I would ask a question; Mark would give an answer that was reduced to the least common denominator. He really seemed pretty… guarded.”

And with that, Victoria’s husband, Stuart, walked in… with the much-needed figurative flashlight.

“I could have told you that! He’s wound tight that Mark. Hell, I’ve known him for twenty years and I couldn’t tell you much about him. He’s all about work.” And with that, he looked at Victoria. “Has he ever had a boyfriend? I don’t think he’s ever had a second date!”.

Victoria shook her head. Of course she knew everything Stuart said was true. The look in her eyes told me she was hoping I would play the part of Geraldo Rivera and pop open the vault.


Going on a date that is arranged by a friend is a great way to meet new people, but doesn’t guarantee that you’ll have a 1FineD8. Set-ups are great because our friends have our best interests at heart, and at the same time having a date with an endorsement is always a positive and stacks the odds in your favor.

Where I made my mistake was that I was wrapped up in the moment of excitement over an endorsed date. That excitement led me down a path where I forgot to ask some very important questions of my own personal Yenta. Next time (and us single guys and gals KNOW there will be a next time!) I will ask the following questions before saying yes to the set-up (and I suggest you do as well!):

•How long have you known this person?
•Did you also know their last boyfriend/girlfriend?
•Do you know why he/she broke up with their Ex?
•Why do you think he’s still single?
•If you were single, would you date him/her? Why?

This may seem like a lot of questions, but in the end it really isn’t. In the world of sales, it’s referred as qualifying your lead. If your mission is 1FineD8, you need to be sure that your partner in dating crime is exactly that- an equal partner. In my situation, Mark wasn’t my equal when it came to communication. If I went into the situation knowing that he was closed off, perhaps I would have augmented my strategy in engaging him to share. There is also a possibility that I would have taken a pass at the opportunity- we’ll never know for sure.

When you hear the five words, “I have someone for you”, please keep those questions in mind and ask them before committing. Who knows… your lead may end up being a fantastic one and before you know it, you’re enjoying 1FineD8!

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s